After All of This Time
by theperksofbeinganauthor
Summary: As Leaf, May, Drew, Ash, Gary, and Misty head to Goldenrod City for various reasons, they find themselves reunited again, competing in the Golden Battling Competition. However, they all end up dealing with an extra challenge they never expected to face: love. Mostly based off the anime. Mainly Leaf/Gary & Drew/May. Minor Ash/Misty.
1. Chance Meeting Part 1

_Hey guys! I'm back. This is going to be my second long-fic, which feels weird because I like writing drabbles and one-shots more. However, I'm trying something new this time around, so I hope you guys enjoy!_

 _I hate being on hiatus for so long, but after two years, I think that I'll be back for a while. I think it's been two years since I last wrote anything about Pokemon. It might seem weird since the first half of this chapter was written about three years ago, whereas the latter half was written this week..._

 _This is a Oldrivalshipping, Contestshipping and Pokeshipping Fanfic. There is not much emphasis on Pokeshipping though, because I want to do the couples justice throughout this story by trying not to have too many things going on at once._

* * *

 **~ After All of This Time ~**

 **theperksofbeinganauthor**

* * *

 **Chapter 1: Chance Meeting Part 1**

Goldenrod City is huge.

There was no doubt about that. It was among one of the biggest cities in the entire world, and it was famous for its confusing roads and luxurious shops. It was known all over the world for its wondrous landmarks and sites. Leaf decided, however, that Goldenrod City was the absolute worst. Out of all the cities she has been to throughout her journey, she had never entered a city as bad as this one. Every crook and corner of this city was either a dead end or another gateway to nowhere. Letting out a frustrated sigh, she sat on one of the benches in the beautiful city.

The last time she came into Goldenrod City wasn't that bad—she wasn't as lost back then as she was now. It probably grew and changed, Leaf figured. She had spent the last hour trying to find her way around the city and to make her way to the Pokémon Center, but that wasn't going to happen anytime soon.

She definitely did not want to admit it, but she had no idea where to go. Asking around didn't seem to help, as nobody actually knew where they were going either. One of the girls that she asked led her into a dead end, so she knew there was no point risking her pride for something like that. Her long hair flowed in the wind, flapping annoyingly against the side of her face. Irritated, she pushed her hair over her shoulder and stood up from the bench.

As if the wind had brought her a rush of inspiration and motivation, she smiled and rushed toward the park, throwing a Poke Ball into the air. If she couldn't get to the Pokemon Center, she might as well be doing something more productive— like training her Pokemon. "Let's go, Sylveon!"

* * *

"I will never ever listen to you ever again. Remind me why I bothered to follow you again." Drew grumbled to the girl, snatching the map away from his companion's grasp.

In response, the girl, May, scowled and frowned. "You were following me because you had no luck in navigating in this city. Apparently, neither can I, so we're in quite a situation," she declared.

"I don't understand how you can be so optimistic during a situation like this. I've been annoyed with this map since we got it, and you're still so carefree, spouting out nonsense about being lost."

From his point of view, he couldn't tell the difference between the buildings anymore. They all look like stupid buildings to him at this point. Besides, that one building looked awfully familiar, which could only one thing...

"May, I think we already took this route," Drew explained in an exasperated tone. He flipped his hair in annoyance. He examined the map carefully, trying to make use of it. It was basically useless since they were going in circles for a whole hour. And to top it off, he had to spend the whole hour... with _her_.

She was the most annoying person he had ever had the misfortune to meet. She would not stop talking when it got quiet, which is understandable, but that meant that he had to respond to her ridiculous means of conversation. She may be annoying, but he didn't want to come off as rude—not to her anyways.

May, who was busy admiring the landscape and tall buildings, frowned. "Yeah, the buildings are starting to look awfully familiar. Where is the Pokemon Center anyways? I'm so tired and hungry that I can eat a whole city."

And there it was. She was hungry... again. "We just ate before we came here… _and_ it got us lost."

However, her stomach didn't seem to agree, as it was growling. "I don't think I can go on anymore. I'm sooo hungry," she whined.

He sighed, glaring at her intensely. "Fine, we'll stop by the park and find a bench to sit on. If we head back along this street, we should hit the park in about five minutes."

May nodded happily, as if she wanted to hug him silly. "Yay! Let's go then!"

"... what happened to being tired and hungry?"

* * *

Sylveon cried out her name and opened her mouth to release the attack. However, a pink ball flew sideways uncontrollably and flew toward the sky.

In response, Leaf just looked disappointed. She was used to seeing this result, but she was hoping for a different outcome. She knelt down onto the floor next to Sylveon and placed a hand on her head, patting it affectionately. "It's alright, Sylveon. You'll get it eventually," Leaf consoled. For some reason, her Sylveon seemed unable to control the move and would always send it flying in different directions rather than the intended target.

"Do you want to take a break now?" she asked kindly. It wasn't fair of her to push her Sylveon this hard when it is doing its best to perform properly.

Sylveon shook her head stubbornly and stood up straighter, determined to attempt it once more. "Alright Sylveon," she shouted happily. "Moonblast! And aim for that tree!" She pointed at a nearby tree, hoping that it would hit it this time rather than skyrocketing somewhere else.

After many tries, they progressively got better... but only by a bit. By the end, the pink ball managed to make its way out of her mouth and narrowly missed the trunk of the tree.

Despite being so sure of himself earlier, Drew had a bit of trouble figuring out the location of the park… especially with May constantly distracting him. "Stop complaining; it's getting annoying," Drew grumbled. He was glad, though, that the park was really starting to become visible as they headed down the road. He did not know how much longer he could handle wandering around aimlessly anymore.

"Well, what else am I supposed to do?" May mumbled under her breath. "It's your fault we got into this mess in the first place."

" _My_ fault? How is this _my_ fault?" Drew argued back, sounding a bit more irritated than before. Being lost around Goldenrod City was not helping their mood much.

"Why you—"

However, before May could finish retorting, Drew tackled her onto the floor without a warning. "Oww, what the hell, Drew—"

The loud crash could be heard to her left; she groaned in response. She might have injured something in the process, but it was difficult to tell with everything happening so quickly. As she looked over, she saw the remains of a tree with most of its leaves and branches knocked down by some unknown force. She scanned the area, but she could not seem to find the cause of the collision. When she looked up, she blushed furiously—completely forgetting that the extra weight on top of her was Drew. She wanted to yell at him for shoving her so suddenly and thank him for saving her from further injuries at the same time, but no words came out of her mouth. Shock and embarrassment seemed to take over all of her senses—making her unable to move or think.

Drew, who finally seemed to have regained himself, finally propped himself up with his palms and looked down. He, too, flushed noticeably, but he appeared to preoccupied with other matters... such as berating the girl who was so oblivious to her surroundings. "Geez, you're so inattentive. Are you alright, though?"

All May could manage at this point was a slight nod, trying not to die from embarrassment.

"Oh my gosh... I am so sorry!" a feminine voice called out from a distance. Even without looking, both May and Drew that she sounded a bit frantic and the light panting in between her phrases suggest that she was running toward them in a hurry. Finally realizing their predicament, they both hopped to their feet abruptly. Hoping that the girl did not see what happened to them would be wishing for too much—apparently. The evident smirk on her face was enough for them to realize that she had seen it all. "Are you guys okay?"

"Yeah," May managed, trying to brush dirt and grass off of herself. Once she was done, she finally looked at the girl who approached them. She seemed to be around her age, yet a little bit more mature. May noticed that she was dressed in a rather cute tank and skirt, with a hat on that covered the top of her long brown hair. "What was that anyway?"

The girl suddenly grew sheepish, laughing awkwardly. "Well, you see... I was practicing with my partner to control her accuracy, but as you can tell, that did not turn out so well." She gestured toward her pink partner, who was hiding behind her legs—ashamed. "Sylveon, apologize to them." In response, Sylveon just bowed its head slightly.

May squealed lightly, bending down to inspect the Pokémon further. "Aww, she's so cute!"

While May befriended the Pokémon, Drew seemed to scowl at the girl who had tried to attack them due to her inability to control her Pokémon. "Tch, that seems like such an amateur mistake—being able to control your Pokémon should be _easy_." Drew's condescending manner was quickly met with an elbow jab from May. She glared at him, silently scolding him— _Be nice._

"Yeah, I am really sorry about that! My name's Leaf, by the way. I am a Pokémon trainer. And this is my partner, Sylveon. Nice to meet you!"

"Don't mind anything this guy says. I'm May, and this is Drew. We're both Pokémon Coordinators," May explained.

Leaf returned Sylveon to its Poké ball and smiled lightly at her new companions. "I think we should head back to the Pokémon Center in case we need to heal your injuries."

"I'm fine though," May tried to protest, but Drew caught her wrist.

"You're bleeding," he stated simply. And sure enough, as she looked down, she noticed a long scratch across her forearm—probably caused by the fall. It was not bleeding extensively, but there were light signs of blood showing up. She had not paid it any attention until Drew pointed it out, as she was too preoccupied with other matters before.

"I'll come to the Pokémon Center with you guys," Leaf offered, walking ahead of them. "I am done training my Pokémon for the day."

"Okay!" May chirped, following suit. Drew had no choice but to follow, but he sincerely hoped that the strange girl that they had just met knew where she was going. If her sense of direction was as good as her skills as a trainer, then they were in trouble...

"So what brings you to Goldenrod City? Something tells me that you two are not from here," Leaf observed.

Drew appeared to have ignored her completely, thinking about something else entirely. May, however, responded to her inquiry. "Drew and I are both from the Hoenn region; we are only traveling back here to participate in the Golden Battling Competition next week."

Leaf exclaimed excitedly, "Oh! Me too! I also wanted to challenge the Gym Leader, but when I heard about the competition, I signed up immediately. I have been staying here for a couple of days to train, but it didn't turn out well, as you can tell..." Leaf sweat-dropped slightly. She then added as an afterthought, "I'm from the Kanto region, but I have been traveling around to almost every region throughout my journey."

"Oh really? I have a friend from the Kanto region too," May replied. _I doubt that you know him though,_ she added in her head. "Oh by the way," she decided to change the topic, "are you sure this is the right way to the Pokémon Center?"

In response, the girl let out an awkward laugh. "To be honest, I have been lost all day, so I'm not so sure. Ahaha... I was sort of following you guys."

"Wait, we were following _you_ because _we_ were lost all day..." May stated slowly, finally putting two and two together. _Wait, that means that..._

In the background, Drew facepalmed and murmured something unintelligible.

… _they were hopelessly lost._

* * *

 _Next chapter will feature the other three characters! :)_

 _Please let me know what you think! I have trouble updating long-fics due to lack of motivation, so I'll update faster if I get more reviews and know that people are interested._

 _I hope to be updating regularly or at least once a month. However, school life and term papers make things difficult to manage. :(_

 _Oh yeah, I am also accepting requests for fanfics if you are interested. Just fill out the form on my profile!_

 _Hope to be back soon,_

 _Lily._


	2. Chance Meeting Part 2

_Happy Holidays! And thank you for all of your support. It means so much! I hope you enjoy the next chapter._

 _And to the anon who told me this is Leafgreenshipping not Oldrivalshipping, thanks for pointing that out. I never really realized that, but I have been basing Gary/Leaf's relationship off of the manga (Blue/Green). Therefore, I almost use those two interchangeably. I mean, honestly, it really makes no difference to me which term I use to label them... I've always referred to it as Oldrivalshipping just because I see them as counterparts to Gary and Leaf and base their relationship off of the manga (obviously because Leaf never really shows up in the anime). But thanks for pointing that out. I'll keep that in mind._

* * *

 **~ After All of This Time ~**

 **theperksofbeinganauthor**

* * *

 **Chapter 2: Chance Meeting Part 2**

"Professor Oak," Ash complained. "Why do I have to accompany Gary to Goldenrod City when he can go there by himself?" He grumbled something about not wanting to help Gary out, but it was ignored by the other two present parties.

"Yeah, Grandpa. I can take care of this myself." Judging from the annoyed tone and the glare he sent in Ash's way, the spiky haired boy did not seem to be pleased about their situation either.

The Pokémon Researcher, Professor Oak, had asked Gary to run an errand for him in Goldrenrod City, but since Ash seemed to be visiting his lab then, he got roped into the task as well—much to their dismay. He returned to his work, ignoring the complaints of the two teenagers who were obviously disturbing his work with their nonsense. "Well, Ash. I am sure you will definitely want to tag along—there is a competition going on in Goldenrod City next wee—"

However, even before Professor Oak could finish his statement, Ash jumped up for joy, almost forgetting his upcoming unpleasant trip with his formal rival. (Even if they were no longer competing for the same title anymore, they still considered each other rivals and competed with each other while doing the most trivial of things.) "That's so cool! I am definitely in! How do I sign up?"

"Well you have to wait until you get there to sign up," Professor Oak elaborated. "However, I recommend going there with Gary if you want to get there faster."

Hook, line and sinker.

Gary knew what his Grandpa was doing, and he could _not_ believe that it was actually working. Obviously, by mentioning the competition, Ash would most definitely agree to go along with him without complaint. And even if he refused to go with Ash, Ash would tag along regardless because it would be quicker (and safer) if the two of them traveled together. He inwardly groaned at how gullible Ash was; to think that they were the same age...

The only reason why Professor Oak was so adamant about having Ash tag along was because he thought that Gary would get lost traveling to Goldenrod City by himself. Gary knew this, but he felt slightly offended that his grandfather thought that Ash's direction sense was better than his. His task was not the most difficult of tasks, but he understood the importance and significance of it: he was asked to transport the trophy of the Golden Battling Competition to the site from Professor Oak's lab.

He knew that there might be complications and troubles along the way so having Ash present would be simpler. Ash's company, though, would be a hindrance though as he was probably terrible with directions. Now, if he had _her_ helping out, he would not mind as much. _Now is not the time to be thinking about her,_ he chided himself abruptly. He quickly shoved that thought out of his head, as he glanced over at his company for the next two weeks—who was trying to hide his excitement while being harassed by his Pokémon. His Muk was trying to pin him down to the ground and squish him while Bulbasaur was desperately trying to pull him away with its vines. Pikachu just watched with amusement.

Meanwhile, Gary stared at the commotion and sighed miserably. _Something tells me that this trip will just get reeeeal fun._

* * *

"Oi, Misty! Don't forget to clean out the tank," Lily hollered as she was leaving the Gym.

"Oh, and don't forget to feed my Pokémon!" Violet demanded, running after her sister frantically.

Misty found herself stuck at the Gym alone—yet again. This was the fifth time this week. Despite agreeing to be the full-time Gym Leader of Cerulean City, she had expected her sisters to help out once in a while. She exhaled loudly in irritation; it wasn't like she had high expectations from her sisters anyway. It would be nice to take a break once in a while though. She was the youngest of all of them, and yet she was the most responsible. Now, how was that any fair?

If she had time to spare, she would probably still be traveling with Ash...

Just thinking about it made her feel upset and nostalgic. It had been a while since she last saw him, since she was just so busy with the Gym, and he was so busy fulfilling his dreams. It would not _hurt_ if he just came by once in a while to visit her... but that was probably asking for too much. He probably forgot about her by now.

She let out another sigh before going back into the Gym to take care of the aquarium. It was not until she began to clean the tank that she realized that Daisy had already begun draining it out. "D-Daisy?" Misty called out, uncertainly. She was not quite sure if she was seeing the right thing. Surely, Daisy would be out and about with the rest of her sisters instead of cleaning the gym.

"Oh hey, Misty," Daisy answered. "I just noticed that you were working really hard lately, so the other sisters and I have decided to give you a little break."

The younger sibling simply stared at her elder sister with a blank look—not quite believing what she was hearing.

Since Misty was not responding, Daisy continued, "We're going to take turns taking care of the Gym for a couple weeks—I guess the others just forgot about it today." She shrugged absentmindedly in between her statement. "Why are you still standing here? You're wasting your freedom."

"B-But..."

"Hey, do you want the break or not?"

"Of course I—"

"I recommend going to the spa or something. Oh hey, I heard that there's a competition going on in Goldenrod City. I think you should take the opportunity to hone your skills as a trainer since you haven't left the Gym in a while. It will be a good chance for you to gain experience outside of Gym battles."

After contemplating the offer for a bit, Misty responded with a smile. "Thank you so much, Daisy! I owe you one!" Misty finally exclaimed. "Tell the others that I am really grateful." This will definitely be an interesting opportunity for her, especially since she would get to improve her skills as a trainer and leave the Gym for the first time in forever. And maybe... she might even see _him_ there. And without a second's hesitation, she ran into her room to pack.

* * *

"Ne, Gary, how's your research going?" Ash inquired after a long period of silence.

They have set off for their journey a couple hours ago. The walk to Vermilion City was not far, but it _felt_ long with Ash's constant attempts at conversation. "Fine," he stated blandly. He was more focused on lugging the wagon with the trophy rather than engage in small talk. It was in a box and covered up with blankets to avoid any problems with passersby.

"Have you caught any new Pokémon recently?"

"Yep."

One-worded responses were the only type of responses that he seemed to be getting. He knew Gary was never one for small talk, but he usually talked more than this. They usually talk about random things—or argue about random things—but Gary was never this quiet. It was difficult to pin point why he was acting the way he was acting, as this was definitely not normal Gary behavior. A quick glance at his face was enough to know that he was deep in thought—thinking about something that was probably bothering him.

"Are you going to compete in the tournament?" Ash tried again.

The answer was almost immediate this time. "Nope."

 _Yep, unquestionably not normal Gary behavior,_ Ash concluded. _Gary would never back down from his challenges—no matter what._

"C'mon, you have to enter the competition too! How else are we supposed to decide which one of us is better at battling?"

"I think that's pretty obvious without battling," Gary snorted with a smirk. It appeared that taunting him had been a successful method of trying to get him to talk.

"Why you—" Ash began, but never managed to finish his statement as the ferry had arrived at Goldenrod City.

* * *

Misty left Cerulean City almost immediately.

It had been a while since she was able to get away from the Gym, and she wanted to treasure it as much as possible. With a grin on her face and a backpack hanging off her shoulders, she hopped onto her bike and set off for Vermilion City.

 _I wonder if I will run into Ash at this competition,_ she thought with a slight giggle. _It had been a while since I last saw him, but I would not be too surprised to see him there. I should not have my hopes up too high though—I heard from Tracey that he has been traveling in some region far away from the Johto region._

Thinking back on their old journey together felt like an eternity ago. She felt a bit nostalgic just recalling the precious memories of her journey with Ash and Brock. _If only I did not have to take over the gym so soon. I wish I was still traveling with Ash..._

* * *

Having finally made their way to the Pokémon Center—after five dead ends and three futile arguments—Leaf, Drew and May decided to take the opportunity to stock up on better maps. They registered for the Golden Battling Competition while Nurse Joy tended to May's wounds. Her injuries were minor, but they still required attention.

"I am so sorry," Leaf apologized once more, bowing dramatically. "I didn't mean to attack you guys out of nowhere like that. To make it up, how about I treat you guys out to ramen?"

May smiled lightly while Nurse Joy was bandaging her arm. "It's no big deal, honestly. And ramen?! That sounds great!" Her mood visibly brightened at the mention of food. She then asked Drew, "You'll come with us right?"

He simply nodded, as he watched the two girls fawn over ramen and bond over other girly things. He followed them both without a word, watching May closely from behind. However, before they stepped outside of the Pokémon Center, Leaf announced that she had to use the restroom and ran off without another word.

"Isn't she nice, Drew?" May asked, directing her attention to her rival for the first time since Leaf's appearance.

He shrugged in response. "A bit careless and amateur if you ask me," he remarked, flicking his hair to the side. However upon seeing her glare, he added, "Though, she is nice."

May seemed to be relatively happy about making a new friend, but she snapped out of her revere the moment she heard two figures arguing loudly upon entering the Pokémon center.

"I _told_ you this was the right way, yet you wouldn't listen to me," the boy that Drew did not recognize snarled. "It's all your fault we walked around in circles even though I knew where the Pokémon Center was.

And although the other figure was not close enough to see, his voice was very distinguishable. _Ash Ketchum._ "How was I supposed to know they changed the streets since the last time I came here?" he argued back, growling in irritation. However, his anger was completely vanished the moment he saw the two familiar coordinators sitting on the couch of the Pokémon Center.

Pikachu seemed to react first as he jumped into May's arms at once, while May and Drew both exclaimed, "Ash?!" It had been a while since they last saw each other.

Ash ran up to the both of them with a wide grin on his face—as if the argument from earlier had not existed. "Hey guys! What are you guys doing here?"

"We're here to compete in the Golden Battling Competition! We were close by and decided to stop by. What about you?"

"Me too!" Ash said excitedly once he realized that he would be competing with his other friends. "See Gary, you should sign up too."

"Pass," he stated blandly, dragging the wagon up to the spot where the other three trainers were standing.

Ash, who was too caught up with May and Drew's appearance, completely forgot that he had not introduced Gary yet. "This is Gary Oak; he is my neighbor, childhood friend and rival. And this is May and Drew—they are both Pokémon Coordinators. May used to be my traveling companion, and Drew is her rival."

"Nice to meet you!"

"It's nice to meet you too."

"W-Wait, you're Gary Oak right? As in Professor Oak's grandson?"

"Yeep, the one and only," Gary remarked proudly.

"Oh wow!" May cried out excitedly. "That's so cool! Tell Professor Oak I said, 'Hello and that the Wartortle he gave me is doing just fine!'"

Gary nodded and smiled, "He'll be happy to hear that." He turned to Ash and gestured toward the wagon he had been pulling around. "I am going to ask Nurse Joy for a room and leave this in there for now. You should go sign up for the competition now before they fill up."

Gary's attitude lifted considerably since he met May and Drew, which was strange indeed. It was a good thing, but Ash could not help shake the feeling that something was off.

Unbeknownst to Ash and Gary, their childhood friend that they had not seen in a while, Leaf, was just around the corner, eavesdropping with a serious look on her face.

* * *

 _Please leave a review. Your feedback and support means a lot! It doesn't have to be long, but it'll make me very pleased._

 _I will still be accepting fanfic requests (link on my profile), so if you are interested... just fill out a form._

 _Also, now that you know the main participants in tournament, who do you want to win? Vote on the poll on my profile (because the results of the tournament will be dependent on you guys!). I'll leave it up there until the tournament ends... which will be a while. So don't forget to vote! (Any vote left in the reviews will not count, but you are always free to leave your opinion in there...) And spoiler alert, Gary, regardless of what he says, will end up competing too. ;)_

 _Lots of love,_

 _Lily._


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